


Jessie for Rent 2

by FestivalGrey



Series: Jessie for Rent [2]
Category: Pocket Monsters | Pokemon (Anime), Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Sun & Moon | Pokemon Sun & Moon Versions
Genre: Dirty Talk, F/F, F/M, Face-Fucking, Face-Sitting, Girls Kissing, Group Sex, Jessie is dominant, Lillie gets fucked so hard she can't speak, Lillie is 18, Lillie's first time, Loss of Virginity, Multi, Oral Sex, Rough Sex, Vaginal Fingering, Vaginal Sex, male reader - Freeform
Language: English
Status: Completed
Published: 2018-11-02
Updated: 2018-11-02
Packaged: 2019-08-14 13:39:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,540
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16493618
Author URL: https://archiveofourown.org/users/FestivalGrey/pseuds/FestivalGrey
Summary: A sequel to Jessie for Rent, commissioned by the same person as the original. Jessie returns to your house with Lillie in tow; can you satisfy them both, especially given it's Lillie's first time? Male Reader; Lillie is 18+ in this fic!





	Jessie for Rent 2

When the door to your apartment raps from fierce knocking, you’re ready. Jessie’s returned, as she said she would, and if she was telling the truth, she brought someone else with her. Looking around at your apartment (still disheveled from the last go the two of you had at each other) you smirk before opening the door.

 

Jessie stands there cockily, her grin knowing and hungry. “Hey there, big boy,” she says coyly, reaching out to brush her hand against your collarbone. You fight down the urge to shudder with need, but only barely. She seems to see your difficulties and grins even more. “Mommy came back for more, like she promised.” She’s changed her clothes into a skimpy dark top and a pair of very tight shorts. The black fabric of her panties ride out of her shorts and circle her hips, prominent enough that you know it is on purpose. “You like the show mommy is putting on for you?”

 

When you affirm, she grins even more. “But look!” she says. “Mommy brought you a cute little sister too!” Reaching into the hall, she pulls in a blushing young woman from out of sight. The newcomer is tall and waifish, her pert breasts the opposite of Jessie’s huge boobs, and her pale yellow hair is done up in a ponytail, a small braid surrounding the base. Two side locks frame her cute, pale face. Near to her whole body is on display—she’s wearing a skimpy black swimsuit, the top cupping her breasts and the bottom little more than a glorified thong.

 

“I—I’m Lillie,” the girl says, obviously shy. She idly pushes her hair over her ear in a nervous tick, looking down. “G-good to meet you…”

 

“My friend Lillie here just had her eighteenth birthday last week,” Jessie says with a laugh, “and on hearing that she’s a virgin, well… I thought, what better present than to get her railed?”

 

Lillie swallows, blushing. “I’ll be a good little sister… promise! So please make it good for me!”

 

Nodding, you back away, letting them enter your apartment. When they’re across the threshold, Jessie sighs with relief. “I want to get started right away, but first I think mommy should get little sis all ready for you. You just sit back and enjoy the show.”

 

Wondering what on earth she could have planned, you take a seat. Jessie’s sultry voice and Lillie’s skimpy attire has already left you stiffening, and you unbutton your pants, letting your cock go free. Lillie eyes it as you stroke.

 

“Eyes up here,” Jessie commands, cupping Lillie’s chin. She turns the girl’s face to hers and you figure out what Jessie is going to do moments before she does it. She surges ahead, her lips meeting Lillie’s, and you hear a slight, muffled gasp of surprise.

 

Jessie pushes her tongue into Lillie’s mouth and the younger woman’s eyes flutter as she moans around it, her voice rising to a high whimper. A moan escapes from Jessie’s lips and she pushes in tighter, her hand slowly traveling from Lillie’s chin up the side of her face, tracing along it with her nails, to slowly thread her fingers through Lillie’s hair. The sound of their tongues squirming and wrestling against each other fills the apartment, and you can’t help but watch with appreciative candor. Your dick feels hard and hot in your hand and without thinking, you grab hold of it and begin to pump.

 

When Jessie speaks, her voice is breathy and sultry, and behind it you can hear Lillie gasping for air. “You like this, lil’ sis?” she croons. “You like putting on a show for your brother for the day?” When Lillie whimpers her assent and tries to push back against Jessie’s mouth, resuming the kiss, Jessie arches her head back, laughing. “Then let’s get things a little _harder!_ ”

 

At the word, the fingers threading through Lillie’s hair suddenly knot up as she tightens them, grabbing a bunch of Lillie’s hair and yanking it up. The younger woman’s eyes shoot open and she lets loose a high-pitched whine that is a mixture of pain and absolute, devious pleasure.

 

Jessie’s mischievous eyes are like firelight. “You might _act_ like a sweetie,” she says, “but mommy knows you like it _rough_.” Keeping her hold on Lillie’s hair, she slowly pulls her head up, making Lillie stand on her tiptoes, and then resumes the kiss. The sight of Lillie’s face—small, blushing, flushed with desire—makes you get hotter than you ever thought you could get.

 

You hammer your cock even faster.

 

Even with her tongue buried in Lillie’s mouth (and you can see the slight bulge as it explores her gums and traces over her teeth) Jessie looks diabolical and loving it. The redhead slowly takes her free hand down to her tight shorts and hooks one finger around the hem. Tantalizingly slow, she hooks it down, teasing it off her hips, exposing more and more flesh and the black panties underneath. You can smell her from where you’re sitting, her attraction making the air in the apartment grow humid with the smell of her desire. From where you’re sitting, you can see the panties are the same ones that started this whole thing, the writing on them stark white against the black fabric: “Rental Mommy.”

 

Smirking, you decide to take matters into your own hands. Still pleasuring yourself, you ask Lillie if she wants something fun to happen to her. Lillie’s eyes sweep over to you, and she holds her gaze there for a brief moment before nodding energetically.

 

Turning your attention to Jessie, you ask if she could help poor Lillie get ready for a fun time. Looking impish, Jessie puts her hand on Lillie’s stomach. The girl flinches at the touch before moaning as Jessie traces her fingers down the bare flesh before reaching the lower part of her swimsuit.

 

“Mommy thinks you’re going to like this one,” Jessie croons, and slides her fingers under the fabric. Lillie’s voice cracks into a sharp and needy whine as she gets fingered for the first time, and she half-collapses against Jessie, leaning against the older woman for support even as Jessie slips her fingers in and out of her hole.

 

“Ahn—I—oh, I— _a-ahn_ —nnnnnngh—”

 

Lillie’s voice is breaking down, becoming little more than a staccato beat of sharp sounds and needy whimpers.

 

“Good girl,” Jessie teases, clearly enjoying the sensation of Lillie trembling against her while barely able to support herself. “Those are good sounds you’re making. Look at how pleased your big bro looks with you.” Lillie manages to look at you, your cock as erect as ever, and seems pleased that you’ve managed to get so hard just from watching Jessie take the lead with her. There’s a wet sound as Jessie slips a finger knuckle-deep into her and she screams out in pleasure. “Gooooooood girl,” Jessie repeats. She pulls her finger out and Lillie staggers back onto a couch, face blushing as she pants for breath. Her eyes are unfocused and she looks barely able to support herself.

 

Jessie turns to you, idly licking Lillie’s taste off her fingers. “We’ll get back to her in a second,” she says, all confidence. “For now, mommy’s going to sit on your face.”

 

Her tone and words brook no argument, and that’s all right with you. You quickly shed your clothes and Jessie shucks hers as well, both of your bodies bright underneath the light. It’s amazing to think you two were fucking like horny pokemon just an hour or so ago—this woman is completely insatiable!

 

And, you realize, you wouldn’t have it any other way.

 

You lie back on your cushions and before you know it, Jessie is sitting right on your face. You reach up to support yourself, grabbing generous handfuls of her hips as you do so. Her cunt—hot and slick and already puffy with arousal and need—is right in your face, the smell almost overwhelming.

 

“Help mommy out,” Jessie says. “Please, mommy needs help. Lick for mommy. _Lick._ ”

 

You comply, dragging your tongue alongside the outside of her folds. Her taste, strong and overpowering, fills your body and makes you shudder.

 

She shudders, too. “Harder,” she grunts between strokes. “ _Deeper._ Mommy wants it deeper.”

 

You find her hole and push your tongue in. Her whole body tenses, and you feel the pressure of her force push down on you. Idly, between furious licks and pushes with your tongue, you realize that your hands are digging into her hips and thighs. There are likely to be red fingermarks by the time you’re done. Somehow, you don’t think Jessie will care. In fact, this might be entirely what she had in mind.

 

Nothing is visible except for her pussy in your face, the bright afternoon light faded to darkness. Jessie has become your world and you ride it out, pushing and playing her hole with your tongue with unmatched vitality, enjoying the sound of her keening calls and cries. Your cock positively _throbs_ with need, and you find yourself pleasantly frustrated at how little attention it’s getting. Both hands are occupied hoisting up Jessie, and the Rocket herself seems too awash in sensation to do anything about it.

 

And then a demure hand touches your cock, sending an electric shock of unanticipated pleasure through your body. Jessie’s voice, chiming with laughter, reaches your ears, and you realize she’s giving instructions: “Yes, like that. Line it up nice and good…”

 

Lillie—for it is the girl, you realize—follows the redhead’s instructions and your cock is lined up even further. You sense rather than feel her position herself over you and then—

 

Heaven.

 

The young blonde’s voice calls through the air like a song as your cock spreads her virgin pussy. The tightness is unreal, and she involuntarily contracts around you, squeezing you even more as her voice hitches an octave higher than before.

 

But then, slowly at first, she begins sliding herself up and down, your cock sliding in and out of her pussy with the motion. She picks up the pace and soon enough is riding you to her heart’s content, the pace consistent and rather fast, considering it’s her first time.

 

You can’t help but find yourself impressed at her tenacity.

 

Jessie is alternately praising Lillie and teasing her; realizing you want her paying attention to you, you slide your tongue out of her hole. There is just enough time for her to shift over you and begin admonishment before the tip of your tongue finds her clit.

 

A single flick is all it takes to send Jessie into a caterwaul of wordless desire, and her body shakes over your face. The scent of her arousal is so flooding that for a moment you almost forget yourself, lost in the sounds of Jessie’s pleasure and the sensation of Lillie still riding your cock. But soon you let your tongue dance over her clit, driving Jessie into further spasms of sheer want.

 

Soon you fall into a rhythm, flicking and rubbing Jessie’s cock at the same time that Lillie thrusts herself down onto your shaft. Jessie’s high moans complete the trifecta, and for a moment in time, the three of you are one—a trio of actors all giving desire to one another in perfect unison.

 

Jessie is the first to cum, her orgasm making her shake and sending her juices over your face. Sliding off of you with a half-hearted mutter of “mommy just needs a second,” it’s just you and Lillie now.

 

With Jessie sitting on you, you hadn’t been able to get a good look at Lillie as she rode you. Now you see her hair is tousled, her cheeks flush with arousal, her tongue lolling in a pant. She’s cast off her swimsuit’s bottom piece, but the top is still stretched tight around her chest; her nipples are standing out against the fabric, firm and erect.

 

Reaching up, you give lil’ sis a good pinch on one of those sensitive nipples, appreciating her soft sound, before taking the lead. Grabbing her, you maneuver her to all fours, like a pokemon, and tell her that it’s time for her brother to play with her. “Y-yes—please— _auwghn! N-nngahh!_ ”

 

Her words are lost in a high call as you slam into her from behind, using her tight hole to your contentment. Lillie’s arms and legs shake as she barely remains capable of supporting herself, instead panting out soft, repetitive sounds of need: “Hnnn, ughn, ahnnnn—gahh!”

 

Reaching your hands through her hair, enjoying the soft touch, you tell her what a good little sister she’s being before yanking a fistful of it back. Her back arches as her head follows your hand back, her tongue sticking out further. Jessie was right, you realize. The little pixie _does_ like it rough.

 

You can feel an orgasm building in you and you begin fucking her even faster in response, your cock slamming her cervix in the back of her pussy. She pushes up against you, grinding herself for her pleasure.

 

“F-fuck me harder,” she begs. “Please…”

 

You comply, and she goes wild.

 

Before either of you can come, Jessie crawls over. Without a word, she puts her still-puffy pussy directly in Lillie’s face. “Lick,” she commands.

 

You fuck Lillie harder than you’ve fucked anyone, and the force buries her face in Jessie’s pussy. The muffled sound of her eating out Jessie fills the apartment, and the Rocket wraps her legs gently around the blonde’s head, keeping her there.

 

You and Jessie meet each other’s eyes and you both grin—with your cock hammering away at her rear entrance and Jessie’s legs wrapped around Lillie’s head, the younger one isn’t going anywhere until you’ve both had your fill. For now, she’s both of yours.

 

Your orgasm crests and crests and with a passionate grunt, you bury yourself in Lillie’s cunt one last time, hilting as your cum floods into her. Lillie releases a muffled wail only for Jessie to grind her pussy against her face.

 

“ _Lick,_ ” Jessie repeats, and Lillie complies—and before long, her tunnel clenches around you as she cums, too, her lithe body shaking as her body milks you of everything you have. When it’s all done, you slide out of her, your cock coming free with a _pop_ as both your mingled fluids slowly dribble free from her young hole. With an appreciative sigh, Jessie pulls back, and Lillie gulps in breath, her face shiny and slick with Jessie’s juices.

 

“Well, Lillie,” Jessie says between heaving breaths, “was that a good first time, do you think?”

 

The poor blonde is unable to muster a word or even a sound of assent, and she resigns herself to slowly nodding, her eyes almost glazed over from sheer delight.

 

Jessie moves her eyes from Lillie’s face to yours. “And you?”

 

When you affirm, a wide grin splits her face. “Like I thought,” she croons. She reaches down, wipes some of her own juices off of Lillie’s still-breathing face, and idly licks her finger clean. “I think this is the start of a very rewarding partnership.”


End file.
